


Monday Morning

by Kagemirai



Category: Supernatural
Genre: Demon Blood Addiction, Episode: s04e16 On the Head of a Pin, M/M, Torture
Language: English
Status: In-Progress
Published: 2015-02-11
Updated: 2015-09-17
Packaged: 2018-03-11 21:54:58
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 6
Words: 20,846
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3334217
Author URL: https://archiveofourown.org/users/Kagemirai/pseuds/Kagemirai
Summary: <blockquote class="userstuff">
              <p>"You got a lot to learn boy, so I'll see you back in class bright and early Monday morning."<br/>Alastair doesn't delay, taking Dean away before Sam and Cas can intervene. He wants his boy back and will do whatever it takes to keep him and drag him back to Hell. Dean fights but how long can he hold out after finding out how far his brother has fallen and exactly what the final seal is.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> So, I know I've read a few things along the lines of a different ending to On the Head of a Pin. I really wanted to play with Alastair more, he is so much fun to write, so I went with it. Although Dean is my absolute favorite character part of me likes seeing him struggling against the darker part of him. Hope you like it, please let me know, I'm still working on the new arc of Expiration Date and Kings of Hell will be finished I'm just trying to figure out how to get to the end on that one.
> 
> Edit: I did some minor modifications. I'll have the next part up as soon as it's ready.

-Alastair-

 

Alastair's hand was wrapped firmly around his throat, pinning him to the rack the demon had so recently occupied. His boy was so perfect in his pain, green eyes wide with fear. The winged rats had given him his boy back and he wasn't one to look a gift horse in the mouth. Of course the angels had broken his boy when they stole him from Hell, it would take time to fix him. He had to be broken apart to be reformed, he smiled and leaned in close, he needed to make this quick.

"You got a lot to learn boy, so I'll see you back in class bright and early Monday morning." He squeezed firmly, hearing the door crash open.

He pulled his prize close before vanishing, no angel, no demon blood tainted Sam, nothing was going to take his boy away from him again. Oh yes, he had felt Sam and that bitch Ruby pull up outside the building. Dean was barely coherent, a few punches to the face would do that after all. The big issue that he was going to face was when he killed Dean to bring him home, he had to make sure he wouldn't be going up and out of his reach. No, that just wouldn't do. There was also the matter of Lilith and her inane plan to break the seals. For the big battle they would need both Sam and Dean but he knew his Deano, he would never say yes to an angel, but he would scream it to a demon before he was finished with him.

"Bastard..." Dean's voice came out slurred, his head rolling slightly on his shoulders before coming to rest against the demon's shoulder. Alastair patted his cheek softly, wringing a hiss from bloodied lips, "What're you gonna do now?" He tried to tip his head so he could look at him better but it was too much effort.

"We have to get you ready to go home. It will take a little bit of effort on your part, think you can give me one hundred percent?"

"Fuck you."

He let out a hissing chuckle, "Oh, Dean, you've no idea how much I missed you." He hadn't taken the human far and they needed to get moving before the rats or his brother showed up and took him away again, "Go ahead and close your eyes, you need your strength for what comes next."

He knew the look that spread across Dean's face, he always wore it when he was struggling to do something, in this instance it was staying awake. It was a loosing battle and the human was easily picked up once he lost consciousness. He had to be careful with him up here, it wouldn't do for him to die prematurely after all. It took some time but he finally found the perfect location, a secluded cabin in the woods. The people living there were easily taken care of and while it wasn't well stocked with his favorite implements it would do for the time being. Dean was lashed to the table with coarse rope while Alastair hummed softly. The human was still unconscious as he gathered knives, forks, anything he could use in his work. Finally he was ready, now he just had to wait for his playmate to wake up.

 

-Dean-

 

He needed to wake up but was afraid. He couldn't remember what had happened, couldn't remember why there was any reason for him to be so scared. He kept his eyes closed, trying to sort through what was going on. The last thing he recalled was Castiel coming and asking him to torture his former master. Alastair. His breathing immediately picked up and he struggled to calm it. Things were coming back in pieces now, he had taken the knife to the demon, poured salt down his throat, doused him in holy water, and he had only received insults in response and the knowledge that he had started the apocalypse. It was his fault.

"Awake yet, Deano?"

That voice sent a shiver down his spine. Alastair had escaped. He remembered now, the demon had gotten out of the trap and pinned him down, beaten him, and taken him away.

"Is it Monday already?" He needed to be strong, he could wait out the demon, wait for Sam and Cas to find him.

He chuckled softly, "Good morning, Dean."

He finally opened his eyes, looking around. The cabin was made of log, rustic and he was tied down to a table. Slowly he tested the ropes, knowing that Alastair wouldn't leave him any wiggle room. The table itself was solid and thick, he could smell the thick scent of blood, iron and meat, Alastair had killed the previous owners. His head tipped to the side, looking out the window. Trees were thick around the cabin, so he was in the woods, at least that was a start.

"Good morning, Alastair." He parroted back

The demon's fingers ran against his cheek before brushing his hair back, "I see you still have some manners, that's good, we have a nice base to work off of."

"What's your game plan? The angels took a lot of time and effort to pull me back up, what makes you think they won't do it again?" His fingers curled into fists, testing the ropes.

"I plan to bring you back home, back to the pit where you belong."

Dean shook his head, "No, I don't belong there." He wasn't sure of himself, part of him felt like he did belong there, that he deserved to go back into the pit.

Those long fingers patted his cheek, "You don't believe that. You deserve it, for all that's happened, for jump starting the apocalypse, for letting little Sammy down. You haven't been able to stop him from sucking down demon blood. You know he's been drinking from that little bitch, Ruby."

He turned his face to the side, away from him only to have his head tipped back, green eyes met white, "Fuck you."

"I know a little secret." He leaned close, his lips pressing close to his ear, "If your brother kills Lilith he breaks the last seal."

No, no that couldn't be true. They had to stop her, they had to kill her, Ruby had told them...Ruby, she betrayed them, she was working for Lilith. He tried to shake his head but Alastair held him firmly in place. Alastair didn't lie. That was one thing he prided himself on, he would pick you apart, bring your deepest fears to light, and drag you to Hell but he would never lie. The demon's fingers slid down his throat, stroking across his skin, working down his chest. The touch was familiar and his body knew exactly what was going on, Alastair was going to reclaim him for Hell.

He began to struggle, jerking against the ropes, "Let me go you son of a bitch." He bit out angrily, "I have to stop Sam."

Alastair's hand jerked back, wrapping tightly around his throat, "No, I'm not letting you go. I carved you, I broke you, I created you, and I will remake you." He picked up a blade, holding it to the light, "Deep breath," Dean drew one in at his command, "and let it out." He let out a shaky breath, "Good boy, let's begin."

The knife slid down, slicing into his shirt, catching against the skin to draw a thin line of red. A hiss escaped his lips and he knew this was only the beginning, start out slow, draw it out, make it last, his lessons filtered through his head. Spidery fingers slid over his bare chest, memorizing his skin. Dean could remember how easily those fingers guided the blade, burned through him, tore him apart. He barely managed to stop himself from shaking, this demon knew him better than anyone, he had to remember Sam, he had to keep him in his mind, he could win.

 

-Alastair-

 

Dean was perfect, unmarred except for that unsightly hand print on his shoulder. The angel had marked up what didn't belong to him. He needed to make him a blank canvas, remove the mark from his shoulder. The issue with that is it would be too much pain too soon and would shock his system. Impatience had never been a flaw of his but seeing Dean lashed down and spread out like a feast across the table made him want to devour him as quickly as possible. He reined himself in, Dean was a banquette and needed to be savored. Slowly he drew the flat of the blade down his chest, tracing his ribs and collar bones. Every few inches he would give it a little flick, cutting into his skin just enough for him to feel it.

"Dean, tell me how you're feeling."

He kept his mouth shut, staring up at the ceiling. Alastair sighed softly, of course he would be stoic, it was his next line of defense behind smart ass comments. He tended to enjoy it when Dean started to run his mouth and he would eventually start to speak, it was only a matter of time. He hummed softly, watching Dean's face intently, seeing the spark of pain in his eyes. He was waiting for the human to become disinterested, to draw back just enough that Alastair knew it was time to move forward.

"I think it's time to move on, don't you?" The blade slid up, cutting along his sternum toward his clavicle, cutting just deep enough that he wouldn't bleed out or die.

A choked sound escaped his lips, his fingers clenching tightly, nails digging into his palms. There it was, he continued cutting, the sounds getting louder as he slowly worked the blade deeper, working up to removing the angel's mark. Dean was being such a trooper, although he was making sounds he didn't move, didn't struggle, he patted him on the cheek, smearing blood across his skin.

"I've missed hearing your pretty voice Deano, let me hear you, your snark. Insult me, tell me to get it over with." He chuckled softly, drawing his hand down over his chest, a scream escaping his boy's lips, "There's that pretty voice. Let me hear more."

"Fuck!" He barely held still, his muscles twitching under the blade, "What're you working toward? You're starting out slow, working me up fast," he let out a low hiss, "you're moving toward something, what is it?"

The demon smiled, "The angel marked something that didn't belong to him." He ran his fingers over the mark, "It needs to be removed."

Green eyes slid down to look at his shoulder, swallowing hard, eyes wide in fear, "Fuck."

He chuckled, "I think you're ready now. Deep breath," he slid the blade under his skin and Dean sucked in a breath, "and let it out." The breath came out in a scream as he began to flay the mark from his body. He was only halfway through when Dean passed out. He pulled the blade back, shaking his head, "How disappointing."

He moved to the sink, cleaning up a bit, waiting for Dean to come back so he could finish. As he was washing his hands there was a ringing, muffled in Dean's pocket. The towel was stained as he dried his hands. He tossed it aside before digging the phone out and opening it, waiting to hear who was there.

"Dean? Where the hell are you?" Sam, this could be fun.

He smiled, "I'm sorry but Dean is a little...indisposed at the moment. Maybe I can have him call you when he's feeling more himself, he's a little under the weather right now."

"Alastair, where's my brother?!" He yelled into the phone making Alastair shake his head.

"You're so much alike, did you know that? So stubborn, always calling for each other. Sam, stop looking like Sammy, no, no don't, Sam would never do that." He mocked, petting through Dean's hair, "I doubt you could hold out as long as he can though. I think you'd shatter like glass if I were to start working on you. You'd be begging for it to end, to know if there was anything you could do to make it stop. Thirty years, it took thirty years for Dean to break, to pick up the blade and slice into others. He was such a good student and he will be again. I would worry more about yourself Sammy. You're being manipulated, did you know that? Ruby, Ruby, she's playing with you, stringing you along. Dean would want me to tell you the truth. If you kill Lilith the walls come tumbling down."

"What are you talking about?"

He chuckled softly, looking over at Dean, he was slowly starting to wake up, "Ruby is working for Lilith. She's been convincing you to drink down her blood and to what end? To make you stronger? What do you think the effects of demon blood are on the human body? Come now Sam, you're smart, think." Dean let out a soft groan, "Quick now, use that noggin of yours." He stroked through his hair, calming him so he could finish his conversation.

"If I drink enough I can take you out."

He sighed and shook his head, "Think Sam!" He hissed, "The longer you stall the more I'm going to hurt your brother."

"She helped me, while Dean was gone." Alastair stayed silent, waiting for him to connect the dots, "She showed up right after Dean was gone. She said she could help me get him back." There was a hard swallow before Sam spoke again, "She never did."

"There you are Sammy boy. She promised and promised and fed you her blood and then you forgot all about Dean, all about getting him back, and she was there and you felt the guilt hit when Dean showed up at your door." He smirked down at Dean who had finally opened his eyes, "Would you like to talk to Dean? If you're polite I'll put him on the phone."

"Please," Sam's voice came out strained, "please Alastair, may I speak with my brother?"

"You may." He lowered the phone to Dean's ear, "Go ahead Dean."

"Please tell me you aren't drinking demon blood." Dean was silent for a moment, "Dammit Sammy, I told you she was up to no good. No, you listen, get to Bobby's and lock yourself in the panic room. Detox off that shit." Alastair could hear Sam yelling into the phone, "Sam, shut up. I don't matter, I can hold out, you need to do whatever it takes to stop drinking demon blood, I mean it." He looked up at the demon, "I promise I won't give up but you have to promise me you'll go to the panic room and stay there." A sigh of relief escaped his lips, "Good, get going. I'll see you later, ok?"

Alastair pulled the phone back, "Goodbye Sam." He ended the call, setting it aside, "Are you ready to begin again?"

He locked eyes with the demon, "Bring it on."

The smile he gave was feral, "There's my boy. Deep breath and let it out." He began to cut again and Dean screamed.

 


	2. Chapter 2

**Summary for the Chapter:**

> Dean makes a deal and Sam hallucinates.

**Notes for the Chapter:**

> I usually don't use the chapter summaries but I had to for this one. Enjoy and let me know what you think!

-Sam-

 

He was shaking as he pulled up to Bobby's place. His phone rang again, Ruby, she was calling nonstop. Her messages had started out vague, hinting at his addiction but in the most recent one she flat out taunted him. He gripped the wheel tightly before pushing the door open, leaving his phone ringing on the seat. Bobby opened the door, shotgun in hand.

"Bobby, I need help." He swallowed hard, "Lock me in the panic room, don't let me out."

"Sam, where's Dean?" The scruffy hunter stepped aside, motioning for him to come in.

His hands shook as he moved inside, grabbing the back of the couch, "I don't know, I talked to him, he told me to come here, please Bobby. You've got to lock me away."

"Ok, ok take it easy Sam." He headed downstairs, opening the panic room for him, "I'll call Dean."

Sam's eyes went wide, "No, don't call Dean." He stepped into the panic room, taking in a deep breath.

"What is wrong with you?"

"I haven't had demon blood in awhile. Whatever happens don't let me out." The door closed, sealing him inside, "Now I guess we wait." He looked down at his hands, "I can do this."

There was shouting outside the door but he ignored it, whoever was out there didn't matter, he needed to get better. He sat down, leaning against the wall, closing his eyes. He could smell it, outside the door, the scent of sulfur and iron, demon blood. His tongue slid against his lips, he wanted it, _needed_ it. Dean, he promised his brother.

"Open the door." Ruby was out there, he could hear her now, "You don't get it, this is how we stop the apocalypse, he needs it to kill Lilith."

"Go away Ruby." He shouted, his hands tightening to fists, nails digging into his palms.

She came closer to the door, "Come on Sam, don't you want to stop her?"

He glared, "Leave me alone! I have to do this." He paused, "Bobby?" There was no answer, "I swear to god if you hurt him I will kill you."

"Easy there tiger, he's fine, didn't do a thing."

"Then let me hear him."

"It's ok Sam, you just focus on beating this thing while I get rid of the demon." There was the sound of a shotgun being loaded and a sigh of relief escaped Sam's lips.

"Easy grandpa, I'm going. Feel better soon, Sam."

He tipped his head back, letting it smack against the wall. His skin was itching, his throat burned, he was so thirsty. There were gallon containers of water stored here and he grabbed one, drinking heavily from it, swallowing as much as he could. It didn't help. He closed his eyes, taking in slow breaths focusing on his breathing so he could ignore the symptoms.

"Hello Sammy." Alastair's voice, why was he hearing the demon?

He opened his eyes, no one was there. Slowly he got to his feet, heading to the cot, maybe if laid down for just a little bit he could focus, get through this. He sank onto the cot, laying on his back and closing his eyes. In and out and in and out. He was under control.

"You know, control is a very tenuous thing." That hissing voice, the demon who was currently torturing his brother. Dean, he could do this, if not for himself than for his brother, "Are you sure?"

He kept his eyes closed, not wanting to see if the demon was actually there, "You're not here, you have my brother somewhere but you're not here."

"Open your eyes, Sammy." He squeezed them shut harder until he heard his brother scream. They snapped open, seeing the demon standing over him, a bloodied knife in hand, "Good boy. Now we can get started properly. Time to find out if you shatter as easily as I said you would." The blade slid down his arm and a cry of pain escaped his lips, "Don't worry, I haven't forgotten about my main project, maybe he can join me and you can see just what kind of animal I've carved him into."

 

-Alastair-

 

There was that blasted phone again. He should have destroyed it, crushed it into little pieces. That piece of plastic and metal gave Dean a little hope that he could get through this, that there was someone coming for him. He gazed down at his patient, Dean was resting for the moment. He had earned a brief reprieve for handling the removal of the angel's mark so well. The rest had come off without him passing out and he had remained conscious after. That was the one wound he had bandaged. Reality was just so unforgiving, you could only harm someone so much before they bled out or died of shock. His boy required far more recovery time and it was frustrating.

"Alastair." Dean groaned softly, tipping his head to look at him.

He raised an eyebrow, "Yes?"

"Is my phone ringing?"

"It has been, yes."

He took a deep breath, "Who is it?"

"I haven't bothered to check, it seemed unimportant at the time." It was ringing again. He sighed softly, picking it up and looking to see who it was, "Bobby."

"Let me talk to him." Those green eyes pleaded with him, knowing he was always a sucker when Dean begged, "Please, Alastair."

The demon looked thoughtful, "I want to hear something from you first."

Dean swallowed hard, a flash of fear in his eyes, "What's that?"

"I want to hear you speak with proper respect." He brushed his fingers through his hair, sliding them down his cheek, his neck, "And don't feign ignorance, you know exactly what I speak of."

The human looked away. Alastair knew what was going on in his mind. He was wondering if it was worth it, a phone call for calling the demon master. He took a deep breath, it was one little word and he could talk to Bobby, he could do this.

"Master, may I please speak with Bobby." Polite, he could do polite but he couldn't hold back the inherent sarcasm that came with it.

The demon answered the call, holding it to Dean's ear, "Go ahead."

 

-Dean-

 

"Bobby? I'm..."

He was cut off by the grizzled hunter, "Dammit boy, where are you? Why didn't you answer your phone? Sam showed up and locked himself in the panic room after telling me not to call you. What the hell is going on?"

"Of course I didn't, I'm being tortured by Hell's Grand Inquisitor. He isn't too keen on letting me talk to anyone." He knew the reason Bobby didn't reply, he was in shock, "Bobby, keep Sam safe, please. You can both come after me once he's better. I can handle this, forty years in Hell, remember?" He had to be strong and Bobby had to think that he could keep it together, "Alastair doesn't scare me." No, he didn't scare him, he petrified him, "Trust me, I'll be alright for a few days. Don't come after me until Sam's alright, ok? Promise me."

"You damn fool idjit. Fine, I don't like it but fine."

He let out a sigh in relief, "How's Sam?" He had to know.

"He's hanging in there. I think he's heading into the worst of it."

Alastair was starting to look impatient, "You've had long enough, hurry it up."

"I have to go, ok? Take care of Sam and I'll see you when you get here."

He didn't get to hear the reply as Alastair ended the call, setting the phone aside, "I indulge you far too much." There was affection in his tone and it made Dean wonder what he had planned next, "I'm afraid that I can't cut into you anymore, you'll lose too much blood."

"So, I guess I get to rest some more?" He knew he didn't get to, that the demon had something in mind.

"Of course not, I thought we could explore some of the other elements of our relationship." He slid his fingers down his chest, touching the raw wounds he had carved into him, "You do remember what finally made you step off the rack, don't you Deano?" He leaned over him, lips grazing his ear, "Why you picked up the blade and carved into her?"

He gasped softly, his body reacting to that voice, to the memory of exactly what the demon was speaking of. The real reason he had stepped off the rack wasn't because of the pain, wasn't because of any torture that Alastair could devise, it was because of the demon himself. He had taken up the blade because it was what Alastair wanted, because he wanted to please the demon. The last ten years on the rack their relationship had changed. Perhaps it had started out as a way to break him, touching him in a way that didn't bring physical pain. Rape was beneath the Grand Inquisitor, Dean had asked for it. If he took up the knife Alastair would give him more and the demon gladly delivered.

He swallowed hard, "I remember."

A nail flicked against a nipple and Dean sucked in a lungful of air, "Shall we explore that again? Of course I won't take you until you ask for it and I'm sure that you will." His tongue flicked out against his earlobe, "You always begged so prettily." His nails scratched over the lines of his stomach, "After you stepped off you made the best sounds, the greatest pleas, I loved listening to you."

This was torture, his body definitely remembered, his length half hard, "I can't forget, how could I?" His back arched slightly, "Even if I had forgotten I'm sure you would remind me."

"Did you let little Sammy know how much you missed me?" He nipped down his throat, beard scraping against his skin, "After you saw me in the pediatrician, did it spark that heat low in your gut, remind you of what that angel stole you from?"

A soft groan escaped his lips, "No." He was lying, every night since he had seen Alastair in that church his dreams had been filled with the better parts of his time in Hell.

He chuckled darkly, biting his shoulder, "Liar."

Dean barely held back a cry, "Fuck."

"Maybe later, right now we have other things to focus on." He licked the bite mark, "Tell me, do you miss it?"

He gasped, eyes half closing, this was harder to resist than physical torture, "Do I miss what?" He bit out, fingers clenching, he could do this.

"Hell, do you miss the pit?" Those fingers were sliding over his skin, finding all of those sensitive places, reminding Dean that he hadn't forgotten him.

He groaned softly, "No, I don't miss it." It was true he missed part of it but he didn't want to go back, he needed to be here, for Sam, for Bobby, for the world.

"Mmm, there's that little part deep inside that misses it. The freedom it gave you. Down there you didn't have to worry about anyone's expectations, you got to enjoy yourself." He moved back up to his ear, "Know what I liked the best?" Dean didn't want to hear it, "When those green eyes of yours started to turn black, swallowed up by the darkness. Another year or two and there would have been nothing for those winged rats to pull back up. Oh, Dean, you were and are my best work." He moved so his lips hovered over the human's, "I carved you and made you, created you into what you were always meant to be. Can you guess what happens now?"

He could feel the demon's breath against his lips and he wanted to close the distance between them, "What?"

"You seal the deal, when you die, whatever kills you, whenever it happens, you return to Hell, your soul belongs to me in the pit."

Dean's eyes went wide, if he closed the distance he would be selling his soul, again, "What?" He shouldn't have been surprised, "You get my soul, what do I get? Ten years? That's the worst deal ever."

"Your prize is the best one ever, you get to return home, you get to be free, to let go, cut loose." He didn't move, waiting for Dean to make his decision.

"Sorry, I'm gonna have to say no."

The demon chuckled softly, "This all comes down to Sammy, doesn't it? You cried for him in the beginning, it shouldn't surprise me that being restored topside all you would care about is Sam. Keep little brother safe, that's your goal in life." He paused, "And if nothing were to come for you in ten, what then?" One hand wrapped around his throat, "Your soul would be Hell bound but your death wouldn't be preordained."

Green eyes narrowed, he knew Alastair wanted him and wouldn't be patient enough to wait until someone caught up to him or he died in his sleep, "What's to stop you from offing me after the deal is done?" Why was he even considering this?

His hand squeezed slightly, "Nothing."

 

-Sam-

 

He had pressed himself into a corner when the door opened. He knew he wasn't finished detoxing, he knew he couldn't leave but he wanted it. Ruby was standing outside the door, staring at him, a smirk on her face. For Dean, he promised his brother he would do this, that he could do it. His arms wrapped around his legs, he buried his face in his knees. Where was Bobby? Why wasn't he here?

"Bobby!" He shouted, digging his fingers into his legs, trying to stay grounded.

"He can't hear you, Sam, you know what has to be done. To save your brother, to stop the apocalypse. You need to be stronger."

He glared at her over his knees, "Fuck you. I'm doing this for Dean, I'm doing what's best for me."

"Oh, Sammy, you really think you can do this? You're weak, pathetic." Dean's voice rang in his ear. He turned, seeing his black eyed brother beside him, "Give in, let go, you can't stop yourself."

Dean had taken Alastair's place torturing him. It was a million times worse because although he was still in pain this demon form of his brother preferred to use words. Ruby scowled at him, stepping forward to stand in the doorway, her arms crossed over her chest.

"What's wrong with you?"

Demon Dean grinned, tipping his head and looking over at her, "You could pin her down, slice her open, and drink her blood. Think of how good you would feel, all that power pouring into you. Azazel really did a number on you, you deserve this for all that you've suffered through. Think of the good you can do. You could have saved Jessica, saved me from selling my soul for you, you could do so much more if you just gave in."

"You're not Dean." He mumbled into his knees, "Bobby!"

"He's not here." Ruby rolled her eyes.

"How'd you get the door open, you can't even touch it." He demanded.

She shrugged, "It was open when I got here. Now are you going to come out or not?"

"No, go away."

"Dean, why don't you strap him down again, get to work." Now his mind was creating both of them.

His demon brother chuckled softly, "No, this is more fun. Sammy can block out the pain, can't you Sammy? Dealing with my little brother takes different ways to make him break." He could feel fingers clench tightly in his hair, jerking his head back, "Isn't that right, Sammy?"

There were footsteps on the stairs and he couldn't help his sigh of relief, "Bobby!"

"Shit." Ruby cursed, ducking away to hide.

The grizzled hunter appeared in the doorway, shotgun in hand, "Sam." He looked inside, "Good, you're still here. When I saw the door open I feared the worst."

Sam took in slow breaths, "Close it, quickly, I don't know how much longer I can stop myself from running out." Once the heavy metal door closed he slumped against the wall, relaxing before another bout of tremors racked his body.

"You're doing good, kid, you can beat this. I'm proud of you."

He smiled weakly at the door, "Thanks, Bobby."

 

-Alastair-

 

His boy was such a treat. There was still too much of a risk in physically breaking him down so he had to rely on mentally wearing him out. Dean was already pressing up against him, his hips jerking slightly as Alastair's hand cupped his length. The human knew how this worked, he had to ask for it, beg for it, before the demon would give him what he wanted. His apprentice looked debauched and they had barely gotten started. His hair was tousled, eyes half lidded, the only thing that would make him look even better is if his lips were swollen from kisses but Dean had refused him for the moment. No matter, Alastair knew that by the time he was finished he would be begging for it.

"Tell me." He nipped his ear before working down his throat, "If you want more you have to ask for it, let me hear you." He pressed down with the palm of his hand, rubbing against his jean covered cock.

Dean bucked, taking in a hiss of air, "Fuck, damn it Alastair, come on." He growled, eyes narrowed at him. He pressed harder and Dean's head snapped back, banging into the table, "You're not playing fair."

He chuckled darkly, "Oh, Dean, when have I ever played fair?" He slowly rubbed his hand up and down slowly, drawing it out, teasing him, "Perhaps your release should be part of the deal. You give me your soul and I let you come."

"Don't do this to me again." He growled as the demon pulled away.

"Come now, you know how this works. I get what I want and you get what you want."

"I want to not be killed the minute I make a deal with you." He lifted his hips up.

Alastair raised an eyebrow, "You don't want to come?" He stepped away, leaning against the counter and crossing his arms over his chest.

"Yes, I do dammit but you won't give it to me." He bit out angrily, "Here's my counter offer, I'll give you my soul if you let me come and you don't kill me or have me killed, deal?"

He looked thoughtful. The deal was good, they would both get something out of it, but he wanted Dean how, wanted to break him fully, turn him completely. He wanted to see those black eyes, wanted to keep him until he would never be of any use to the angels again.

He let out an exaggerated sigh, "Very well." He pushed off from the counter, leaning over so his lips hovered over Dean's, "Show me how much you want it."

The human lunged up off the table, sealing their lips together, his tongue flicking out against his lips. Alastair returned it, nipping and sucking, making them swollen just the way he wanted them. Dean was panting for breath when he finally pulled away. Long fingers traced his apprentice's lips, he belonged to him, once again he was in possession of the Righteous Man and he would never let him go again. He grinned down at him, Dean would hate himself in the morning. With a flash of the blade he cut the bindings holding down Dean's legs, pulling his jeans off in one smooth motion.

"Come on, do it." He bit out, green eyes looking up at him, challenging.

A bottle of oil sat on the counter, he needed to work him open, Dean needed to enjoy this, there could be no regrets. Slick fingers found his prize, working to press inside, his boy was a virgin again, the thought practically made him giddy. Every day in Hell Dean was remade anew to start again but it wasn't the same, it was never like the first time. This was the beginning all over again and he couldn't wait to sink into him. Dean growled, lifting his hips up demandingly. Of course he would oblige. He slicked himself and snapped in deeply, feeling him open around him. His muscles clenching and fluttering over him.

"Fuck." The human tugged at the ropes pinning his wrists to the table, "What, did you pick the biggest guy you could find?" He bit out, trying to catch his breath.

Long fingers closed on his hips, "I chose what I found appealing." He snapped in deeply, leaning forward and sealing their lips together again, biting sharply at his lips, "What I knew you would find desirable." He bit down his throat, his hips snapping forward, beginning to reclaim him. Dean would never forget who he belonged to.

His boy was a wild thing, bucking off the table, trying to thrust down against him, taking him in. The demon pounded into him, nipping and biting at his throat and shoulders, branding him with bruises. This was how it should be, it never should have changed. His fingers closed around his length, stroking him quickly.

"Come now Dean, show me how much you've missed me." He hissed lowly in his ear, knowing just how to set him off.

He jerked, clenching around him tightly as he came, his head tossed back, baring his throat to the demon. Teeth sank in harshly as he began to fill him, his fingers leaving bruises on his hips. Yes, the demon decided, this was Heaven.

 


	3. Chapter 3

**Notes for the Chapter:**

> This chapter was going to be huge! Like over 9000 words huge, so it's being divided into chunks. You get one now and then the rest will come after an update of Expiration Date. I said I was going to alternate. If you really don't want to wait anymore let me know and I suppose I can go against my schedule. On another note, I fell off my horse today (5'3'' is a long way to fall), so I'm taking some pain killers and may be a little loopy. If there are any mistakes I sadly can't blame them on this. Nothing is broken and no concussion, just really, really sore. I hope everyone is having a wonderful spring break and please let me know what you think.

-Sam-

 

Sam's mind was finally clear, for the first time since Dean's death he could think straight. He looked up at the door, he could finally get out, he just had to wait for Bobby to come check on him. There was no way to tell how much time had passed since he had last seen the old hunter but he should be coming soon.

"Sam?" Bobby sounded weary and tired, "You alright, son?"

He smiled, happy that he could finally get out, "Yeah, Bobby, I'm good. I feel much better."

The door slid open to reveal a very relieved surrogate father, "Had me worried there for awhile." He hugged him tight, "There were a couple times where I thought you weren't going to make it."

He hugged him back, "I'm good, now we just have to find Dean. Have you talked to him? I know you called him even though I told you not to."

Slowly he pulled back, "He didn't sound too good. He said he'd be fine but Sam, that demon that has him, what do you know?"

"Not much, just that they have a history. The first time we saw him was in that church with Anna. Dean knew him, he was scared, but you know Dean, he'd never admit it. I think they knew each other in Hell. We need to find him, fast." He slid past him, heading upstairs, "We need to track his phone."

 

-Dean-

 

A soft groan escaped Dean's lips, his arms were still bound to the table, and his body ached. Alastair was leaning against the table, cleaning the tools he had been using. He had made a deal, with Alastair. His eyes clenched shut tightly, he was going to Hell, again, and it was because he was an idiot and all he wanted was for Alastair to let him come. He thumped his head back on the table drawing a soft chuckle from his demonic companion.

"Good evening, Dean." He looked back at him, holding the blade to the light, "How're you feeling?"

"Did I really make a deal with you?" He turned his head to look at him, "Why do I feel like you got the better deal?"

Alastair laid the blade aside, "Because I always do. You know exactly how my deals work or have you forgotten?"

He grumbled softly, "I guess I forgot."

"One of the many things you seem to have forgotten." He turned, looking him over, "Since I have your soul I suppose I can put a halt to our session, unless of course you'd like to continue?"

"What I want is to be untied so I can find Sam and we can stop the stupid apocalypse."

He chuckled softly, "You already have, all you have to do is not kill Lilith, nice and easy, isn't it?"

He grumbled, rolling his eyes, "Sure, easy, especially when she's trying to kill us."

"You know she won't actually kill you, she needs you alive." He sighed softly, "It would be far easier if she would just kill you." His grin was feral, "You could join me downstairs much sooner."

"What was our deal, exactly?"

"I own your soul, you got that release you so desperately wanted and I can't kill you or have you killed."

He let out a snort, "Yeah, you got the better deal. Sure, you can't off me but I'm Hell bound. Even if I die I can't escape you." Green eyes met grey, "Before I was knocked off by that hellhound, how long did you know I was coming?"

"Oh, Dean, I've wanted you strapped to my rack for a long time. Those rare moments when daddy talked he would laugh and look me in the eyes before saying that he got the better deal because his boys were up top and they were making a difference. I knew about you before then, of course, how could I not? Azazel and his _special_ _children_ , he overlooked the best of the bunch. So focused on little Sammy for his big plan but you, you were the real prize. I don't know how he could have overlooked the potential in you. Even as a child there was a certain spark, he may not have seen you but I did. I've wanted you on my rack since you were a child and I get to have you, not once but twice. This is quite the treat for me."

"So, you're my creepy stalker?" He tugged at the ropes with a sigh.

"Oh, Dean, the things I'm going to do to you. What we did in those forty years was just the tip of the iceberg. I've had a long time to plan and I can't wait to have you back downstairs. How long do you think it will take you to break this time? Ten? Twenty? Perhaps you'll break right off the get go, Deano." He patted his cheek softly, "Mmm, your brother is on his way, should I leave you naked or return a little bit of your dignity, decisions, decisions."

He closed his eyes and took a deep breath before opening them again, "Please, master, give me my jeans back."

He smiled, picking up his jeans and sliding them back on, "I'm so pleased that you remember how to properly address me, can't have you forgetting your place, now can we?"

A soft sigh of relief escaped his lips, "No, master." It had been so much easier as a demon to call him master, to bow to his wishes, as a human it was almost painful.

"Now, what are you going to tell dear Sam when he finds you?"

What could he tell Sam? He looked up at the demon, "I can't tell him I sold my soul just so I could get off." He looked away, feeling ashamed, "I'll just tell him you tortured me, tried to get me to break again, to go to Hell."

A soft chuckle escaped his lips, "Oh, Dean, but you did break and you are going back to Hell, it's only a matter of time."

"Yeah, well, I don't plan on dying any time soon and that gives me plenty of time to get out of our deal." He glared up at him, "Plan on staying to see my brother? Want to see if he can kill you before you kill him."

The demon leaned down, kissing him harshly, biting at his lips, "Killing your brother just wouldn't do, now would it? No, I'm going to leave you here but don't worry, I'm sure we shall be reunited in the near future." With that he turned and left.

Dean sighed, thumping his head back on the table. Alastair was too good with knots, he would have to wait for Sam to cut him free. Thankfully he didn't have to wait long, Sam and Bobby burst through the door, the demon killing knife firmly in Sam's hand and a shot gun in Bobby's.

"About time you got here, cut me loose, Alastair took off, I'm not sure when he'll be back." The moment his hands were free he stretched, only to bite back a hiss of pain. His shoulder throbbed, reminding him that he was missing a rather large chunk of skin, "Damn."

"Dean, what happened?" Sam was leading the way out.

"He tortured me, wants to take me back to Hell." He rubbed his wrists, "How're you doing Sam?" He slid into the passenger seat of the Impala, his shoulder hurt far too much to drive.

"Better." He paused, looking at Dean's shoulder before starting the car, "Need a doctor?"

He let out a snort, "What're they going to do for flayed skin?" He looked back at Bobby, "Sorry to throw all this on you."

He shook his head, "You two are idjits, you know that right? I wouldn't be here if I didn't want to be." He thumped him in the back of the head lightly, "Just because you were tortured doesn't give you a pass to be an idiot."

Dean shook his head, chuckling softly, "Glad to have you, Bobby."

"What's the plan? Lilith is still after us, still breaking seals."

"She's not going to kill us and she can break all the seals she wants as long as she doesn't die."

"Can't someone else just kill her?"

Dean shrugged, "The knife and angels can't kill Alastair, she has white eyes like him, so I bet the same goes for her. You hopped up on demon blood is probably the only thing that can." He looked at Sam, "So, keep clean and we're golden."

They rode in silence the rest of the way to Bobby's. Dean's shoulder constantly throbbed, at least it kept his mind off his impending trip downstairs. He was worried that Sam would notice something was wrong aside from his shoulder. He was sure that Sam could see the taint Alastair left on his soul. The moment they stopped he was out of the car and heading for the door, he needed to get his wounds cleaned and taken care of, at least that's what he was going to tell them if they asked.

Sam ran after him, "Dean, do you need help?"

He shook his head, closing himself in the bathroom, "Going to take a shower, you can help me after I'm done." He felt sticky and wanted to be clean but it was going to hurt, a lot.

He stripped off his jeans before pulling the makeshift bandage off. Blood covered his body from the various cuts Alastair had made and his shoulder was the worst. It was raw and red, he couldn't remember the last time he had a wound this bad. He turned the water as hot as he could stand before getting in. His teeth clenched in pain as water pounded against him, it burned, and he wasn't sure how long he could stand it. The fresh blood sliding down his shoulder was a clear sign that he needed to get out. At least he felt a little cleaner. He slung a towel around his waist before opening the door for Sam.

"Ok, come play doctor." He plopped down on the toilet seat.

 

-Sam-

 

He had never seen Dean this badly hurt before. His right shoulder was completely flayed, he was surprised his brother was still conscious. Using a soft rag he gently dried around the wound, being careful not to hurt him. Antibiotic and a nonstick pad came next before being securely taped down. The wound down his chest required stitches, as did a few of the other cuts. How was Dean not in shock? How was he not screaming? Every now and then he would let off a soft grunt, his eyes clenched shut tightly.

"Dean, I know you don't want to talk about it but I need to know what happened in Hell, what happened in that cabin." He was carefully stitching a wound as he spoke, at least in doctoring him up he couldn't go anywhere.

One green eye opened to look at him before closing again, "You don't want to know. Hell isn't rainbows and puppies and Alastair is no angel." He sighed, "Alastair was my god in Hell, my torturer. Every moment was filled with just him and me. I broke down there, I did things..." He trailed off, opening his eyes to look at Sam, "He took me to that cabin and he tortured me. He cut Castiel's mark from me, brought me back down to his level. Monday morning, bright and early, that's what he wants, Sam, he wants me back downstairs."

Hazel eyes met green, "He can't have you."

A bark of bitter laughter escaped his lips, "What he wants he finds a way to get and he wants me. He told me things."

Sam interrupted, "Demons lie."

"No." He shook his head, "Alastair never lies. If the angels hadn't grabbed me when they did there would have been nothing left for them to snag. A few more days, weeks, I would have been one of those black eyed bastards." He was hiding something but Sam wouldn't press, "I started it. When a righteous man sheds blood in Hell." He looked down at the bloody rag Sam and tossed on the floor, "I broke and I bled, I took up the knife..." He looked away, his mouth sealing shut.

"Dean, you're here now, you're safe, and I won't let him or anyone else have you."

Dean locked eyes with his brother, "I really hope you don't get disappointed, Sammy."

 

-Alastair-

 

He had been thinking about exactly how he could get Dean down here without breaking their deal. Someone else would have to be responsible for his demise. That would involve someone coming to him, someone mentioning the deal, someone arranging his demise. For the moment he was stuck breaking seals until he could collect his boy and take him back downstairs. He twirled his blade between his fingers, an opportunity would appear at some point, he just had to be patient.

"Alastair!" Crowley, he hated that voice, "You have to tell me something, I must know."

He raised an eyebrow, looking at him over the blade, "I'm afraid I have no idea what you're talking about."

"Dean Winchester." He stated, "How did you get him to sell his soul, again?"

There were other demons present, well, the opportunity showed itself sooner than he thought it would, "I merely showed him what he was missing."

"If you showed him what he was missing, why didn't he come now?" He narrowed his eyes, looking at the white eyed demon, skeptical.

"Sam of course, you know the big plan for him after all. I just have to be patient, I'm sure someone will kill him soon, he is a hunter after all. Such a dangerous vocation." He paused, "I'm looking forward to his arrival of course, the wait is practically murder."

Crowley smiled, "I'm sure you'll see him soon. Hunters make a lot of enemies and those boys are some of the best. I'm sure something will catch up to him sooner rather than later."

He chuckled softly, "The suspense is killing me."

 

-Dean-

 

Lilith was laying low, apparently she didn't like the fact that they had way laid her plans. Ruby hadn't shown back up, which was good because Dean was going to off her the moment they crossed paths again. There had been an influx in demon activity and all Dean could think about was the fact that if he died he was going to Hell. Alastair wouldn't do anything to risk breaking his part of the deal so they weren't sent by him, but someone wanted them dead. Of course that wasn't anything new but it didn't happen this constantly, he hadn't even gotten to enjoy a piece of pie.

He looked over at Sam, he was going to have to tell him something, prepare him for what was coming, but he didn't know what to say. He could leave it be, let Sam think he was sent to Heaven. Wouldn't that be better? They were going to have to move soon, if the demons wanted him dead they were going to have to work for it.

"We should head out in the morning, getting close to our limit in staying here for so long." Sam nodded absently, eyes glued on the pages in front of him, "Hey, Sam, I'm talking to you, what're you reading that's so interesting?"

He looked up, "Looking for ways to bind a demon, that way we can get rid of Lilith without killing her."

"Find anything good?" He laid back in bed, shaking his head.

"Yeah, so, a demon can be trapped in whoever they're possessing, we saw that with Meg. All we have to do is trap her and then bury her or something, cut her into pieces and scatter them, just so long as we don't kill her. I figure so long as she's trapped in a meatsuit and bound to it she can't die. Since we don't know how to kill her, I feel like it's safe to say dismemberment won't."

"Whatever we do it'll have to be quick. Lilith is priority, we take her out of the picture then deal with anything else." Of course he was talking about himself, he might wind up dead before they could take her out.

"We have to find her first, with all the demons coming after us one of them has to know where she is." He laid his book aside, "Let's head out tomorrow and see what we can catch."

Dean nodded, "Alright, deal."

At morning they moved on, heading west toward Wyoming. The demonic signs were a little more pronounced there and it would be the perfect place to set a trap. Dean was kind of hopeful that it would be Ruby that they snagged, he really wanted to get back at her for turning Sam into an addict. For once they let their location be known, made it obvious exactly where they were going to be. A devil's trap by every entrance into their motel room, each of them hidden as best they could. Now all they had to do was wait.

On their drive to Texas the demons had found them easily, there was definitely something that was allowing them to be tracked. Part of Dean was worried, maybe it was the deal that was drawing them in. They shouldn't be coming to collect, not unless someone was sending them. He had no way to know who and no way to get them to stop unless he could get ahold of Alastair, even then it was a crap shoot. The torturer was probably ecstatic that people were trying to kill him.

Dean turned his attention to the TV, Doctor Sexy was on, at least he could be entertained while they waited for the trap to spring. Sam headed for the shower, mumbling something about starting to smell. At least he was pretty sure that's what he said. The sound of the TV and the shower lulled him into a half asleep state. It was nice, just drifting a bit, waiting was boring, it let his mind wander far too much, and right now that was the last thing he needed.

Finally the door opened, it took them long enough. He turned his head to see what they'd caught and was pleasantly surprised, "Ruby! Long time no see! What brings you here? Sam should be out of the shower soon, I'm sure he'd love to see you. Especially after what you did to him." He swung his legs over the side, stretching and getting to his feet, "Any buddies with you? Kind of left an open invitation."

She glared at him, "No, I talked them down, figured I could come see you, talk some sense. You're both crazy, you know that right?" She crossed her arms over her chest.

"Talk sense into us? You're the crazy bitch that got Sam addicted to blood." He grinned, "Well, looks like we get to have a little Q&A session." He rubbed his hands together.

"Ruby?" Sam had finally finished in the bathroom, "I'm not surprised you want to kill us too." He sighed, sounding resigned.

She smiled at him, "I don't want to kill you, I'm here to help. The others, they want to kill your brother. You should be thanking me, I stopped them this time." She looked at Dean, "You have to kill Lilith and the only way is for Sam..."

Dean snarled, "We don't have to kill her, in fact killing her would be a bad idea, but I think you know that." His eyes narrowed at her, "I bet you're in on it and trust me when I say that you're going to tell us everything."

She snorted, "You're wrong. Sticking me in a trap, think that's going to make me do anything?"

"If I have to I'm going to torture you."

"Ruby, please, tell us where Lilith is." Sam moved to the edge of the trap, "You have a chance to help us, take it."

Her smile fell, "If that's the way it has to be." Her eyes narrowed, "We want this to happen and will do whatever it takes." She looked at Sam, "You have to kill Lilith, don't you see? Please Sam, Lilith has to die."

"If you want her dead so badly, tell us where she is."

She shook her head, "You're the only one that can kill her! The knife won't work."

"We'll cross that bridge when we get to it, tell us where she is."

Dean rolled his eyes, they were getting nowhere, "Sam, mark her up so she can't smoke out, I'll get it out of her one way or another."

Sam held up a hand, "No, Dean, there has to be another way."

"Don't get all sentimental on me, we've tortured demons before, this isn't any different."

"I'm going out, do whatever you need to, I can't be here if you start cutting her." He grabbed the keys to the Impala and left.

Dean sighed, turning his attention to the demon, "Easy or hard?"

She smiled, "Crowley let slip about your deal. So you're going to Hell when you die? The other demons have really got your number. They want to be the one to kill the great Dean Winchester."

He picked up his knife, moving to the edge of the trap, "Give me your arm."

"No, why should I?"

"Because you don't want me to step in there with you." He paused for a moment, "Ruby, I'll tell you about the deal if you give me your arm." She held her arm out and he cut the binding symbol into her, "Alastair, he wants me back in Hell and he did whatever it took to get me to say yes. I'm sure you know how persuasive he can be." He scuffed out a line in the trap, grabbing her and pinning her to the bed, tying her up quickly.

"Oh Dean, I never knew you were so kinky."

He smiled, "Oh, honey, there's a lot you don't know about me."

She smiled up at him, "Alastair, what's he going to do with you when he gets his hands on you?"

"Probably the same thing I'm about to do to you." He examined the blade before beginning to cut, "You know, we'll never be able to stay in this hotel again because you wouldn't just open your mouth and tell me where Lilith is."

She took in a hiss of air, "Promise me you'll kill her and I'll tell you everything."

He smiled darkly, "You'll tell me everything regardless." He set to work.

 


	4. Chapter 4

**Notes for the Chapter:**

> I am working on a project this month that is taking all of my writing attention. So, I thought I would give the rest of what I have written for this to tide people over until I can get back to work on this and Expiration Date. I'm splitting this into two parts so you get two updates today. Please let me know what you think.

-Sam-

 

He couldn't face what his brother was doing but only because of who he was doing it to. He still felt for her, even though he knew the truth. She had been there for him after loosing Dean. What he was worried most about was what smelling and seeing her blood would do to him. Part of him still wanted it, that high, that power, he liked how it made him feel but it changed him. He could see that now. He supposed he should consider himself lucky, Dean had unearthed the truth, and now he was sitting in the Impala. How long would it take for Dean to get the information they needed? He wished he knew more about what his brother had gone through in Hell but he was tight lipped about it. From watching him interrogate monsters recently he had noticed a distinct difference in style. Dean had always been good at it but now he was even better. Creatures were talking faster than ever. Sam was positive that Dean's new skills had come from Hell.

His phone was ringing. He scrambled for it, finally flipping it open and holding it to his ear, "Dean?"

"I got her location, why don't you come on back while I get cleaned up."

It couldn't have been more than thirty minutes since he left, what had he done to Ruby to get her to talk? He threw her into drive and headed back to the motel. The smell of blood was heavy in the air as he headed for their room. Slowly he opened the door, not sure what he expected to find. Ruby was gone and Dean had cleaned up as best he could but one of the beds was stained red, it was practically soaked in blood.

"Dean?"

"Be out in a minute, Sammy." He was true to his word, stepping out dressed and clean, "Ready to head out? We shouldn't stay here."

Sam took a deep breath, "We need to talk." He stood firmly just inside the door, eyes locked on his brother's.

"What about and can it wait until we're on the road?"

He needed to get away from the smell of blood, "Yeah, let's go." He grabbed his bag, quickly moving back to the Impala.

Dean went at a slower pace, getting into the driver's seat before driving off, "What did you want to talk about?"

Sam took a deep breath, "Hell, I want to know what happened. Dean, I need to know. You've changed and don't give me that bullshit about not remembering."

Dean's fingers curled tightly over the wheel, green eyes locked on the road ahead, "Why do you want to know?"

"So I can understand."

The laugh that escaped him was bitter, "You really want to know?" Sam nodded, "Don't say I didn't warn you."

 

-Dean, Hell, 40 years ago-

 

He was hanging by hooks and wires, his skin pierced and drawn taut. The hellhounds had torn him apart, killed him in front of his brother. Who knew they worked so quickly, one moment topside, the next hooked up and stung out in Hell. He had cried for Sam, screamed his name until his throat was raw, but no one came. He wasn't sure how much time had passed since his arrival but it felt like forever. He had to stay strong, Sam would be looking for him, trying to get him back, he could hold out, besides, if this was all they had in store for him it would be a cake walk. His body was already growing numb, the pain dulling, he could do this.

Then a demon came for him, slid the hooks free and carried his prize to his work room.

The demon had chosen a male form, his body lithe, his features slightly sunken but attractive in their own way. He carried Dean with ease, depositing him on what looked like some kind of metal table, before strapping him down. It shifted form at his command, lifting him up at an angle. Not a word escaped his lips as he examined his tools carefully, holding each to the light, making sure they were in perfect condition.

"So, I was hoping for some room service, I could use a hot bath and a nice juicy burger." He didn't like the silence, especially not when the demon didn't seem to actually be doing anything.

The demon's lip curled into a smile, "Dean, I was wondering when that famous mouth of yours was going to make an appearance." His voice was low and lisping, dark and full of malevolence.

He shrugged, "Yeah, well, it was too quiet in here."

The demon turned to face him and gave Dean a look at his eyes, his very white eyes, like Lilith, "I suppose greetings are in order. I'm Alastair and I have a feeling you and I will get to know each out quite, intimately over the coming days, weeks, years, how ever long it takes, Deano."

"How ever long what takes?" He tugged at the shackles holding him down, the metal biting into his skin.

"You're special Dean, I'm going to make you an offer. If you step off my rack and take up the blade, cut into souls the way I'm about to cut into you, the torture will stop. You get to either torture or be tortured. What do you say?" He held out the blade, smiling.

His lip curled into a snarl, "I say, fuck you, take your deal and shove it up your ass."

That smile seemed to grow, Alastair seeming immensely pleased with his choice, "Wonderful, let's begin." The blade slid beneath his clothes, cutting them easily from his body until he was completely naked, "Mmm, you're a nice blank canvas for me to work on. Your scars tell so many stories I'm sure, let's see if we can make nice fresh cuts to add to those stories. Perhaps you can even tell me how you got each of them." The blade barely bit into his skin as the demon began to experiment, finding each spot that made him cringe, that made him take in a hiss of air, "Today is more trial and error, things will improve as I get to know you, hmm, unique situation. I like to tailor my torture to the individual, it's the only way to get real results."

Dean let out a grunt as the blade slid just above his groin, digging in slightly deeper, "You get your rocks off torturing people, get them to talk, for what? Step off and join me? Yeah, I don't think so buddy."

"I do so enjoy hearing your voice. I want to hear you scream, Deano. I want to shatter you so completely that when I rebuild you, you will be a completely new kind of animal." He leaned in close, whispering in his ear, "It will happen, you will break, and when you do I will welcome you with open arms to the other side of the rack where you belong."

He shook his head, "Yeah, sorry buddy, never happening, so why don't you get this party started, I'm getting bored." No, he was getting scared but he couldn't let on to that fact.

Alastair patted his cheek, "Enough foreplay then, very well. Let's start with the basics, shall we? Tomorrow is a new day and we can experiment a little more."

The blade bit into his cheek, sliding down his throat. It took a moment for the blood to begin to flow due to the sharpness of the blade. The pain stung through him but he kept his mouth shut, teeth clenching tightly together. The blade slid deeper with every cut, seeking to wring out a sound from Dean's lips. Finally he screamed and Alastair smiled, leaning forward and licking the blood from his cheek.

"There's that pretty voice, come, sing for me some more." It felt like forever before he finally stopped, leaving Dean hanging in his shackles gasping for breath, his body covered in blood, "You're quite the trooper Deano, didn't even pass out once. There are a few things I have to take care of, but don't worry, I'll be back soon." He patted his cheek causing Dean's breath to hitch from pain, "Rest a little and think about exactly how long you want this to continue." He turned and left, leaving Dean hanging limply in his shackles.

 

-Dean, Present-

 

He hated remembering this, hated that Sam demanded he tell him. His brother was silent beside him, not a sound had passed his lips since Dean started talking. He was going to have to continue and eventually he would see the pity in Sam's eyes as he discovered that Dean had broken.

"I need a drink." He pulled into the parking lot of a bar. He would have much rather found a liquor store, there was no way he was going to keep talking about Hell in a bar, "We drink a couple, then come back and I'll tell you more." He got out, heading inside without another look back, knowing that Sam would follow.

He sat at the bar, Sam beside him, and proceeded to drink. Three shots later and Sam was resting a hand on his shoulder, "Dean, I know it's hard but..."

Dean let out a snort, "You have no idea how hard it is, Sam. Just give me a minute." He shrugged his hand off, taking one more shot before leaving. It took Sam a little longer, Dean was sure he had stayed to pay, but soon they were on the road again, "The longer I was down there, the more creative he got..."

 

-Dean, Hell, 20 years ago-

 

"Good morning, Dean."

It was the same as every morning for the past 20 years, "Good morning, Alastair." But he had learned that being polite was far better than mouthing off.

Alastair smiled, "I'm glad to see we're learning. What shall we do today? Are you going to step off the rack or shall I continue?"

He swallowed, he wanted it to end, didn't want to be strapped down anymore, but he had to remember Sam, his brother was still looking for him, wasn't he? He took a deep breath, "Bring it on."

"Very well, deep breath," He waited for Dean to breathe, "and out." On the exhale he slid the blade slowly beneath the skin of his left shoulder, "We're going to get down to the nitty gritty, see what makes you tick. Will you scream for Sam again or daddy?"

He slammed his head back against the rack, letting out a grunt of pain, trying to hold back his cries. Alastair worked carefully, methodically, drawing out every sound of pain he could until finally Dean cracked, just a little, "Sam! Fuck!"

The demon smiled, tearing another strip of skin from him, "Oh, Deano, I'm sorry to disappoint you but little Sammy isn't coming. Remember what happened last time you called for him?"

He clenched his eyes shut tightly, there was no way he could forget. Alastair had taken on his form, had cajoled and comforted him, before tearing out his heart. His teeth clacked together, he couldn't call for Sam, couldn't go through that again. He just wanted it to stop.

"Screw you." He bit out, gasping softly as the blade was taken away.

Gentle fingers ran over his face, the first soothing touch he had felt in what seemed like forever. His eyes fluttered closed as he went limp, reveling in the nonviolent touch. Alastair stroked down his throat, ghosting over his shoulders before moving up and petting through his hair.

"Shhh, easy, there." Tears flowed down his cheeks and the demon was more than happy to lap them up, "Now, is that so difficult? Relax, there."

What was he doing? He had to be on his guard, he could be playing him again, but it felt so good, "What're you doin'?" He mumbled softly, slowly opening his eyes to look up at him.

"You're trying so hard to fight, wouldn't it be easier to let go? Not have Sam or daddy hanging over you, to be your own man. Come now, take the deal, step off the rack. I will treat you better than your so called family." His fingers continued stroking through his hair as he spoke.

"No, no." He shook his head, "Not gonna break, not doing anything to help you assholes."

Alastair sighed, "I'm afraid that's the wrong answer. Let us repeat the lesson."

 

-Dean, Present-

 

He couldn't look at Sam, couldn't stand to see the pity he knew would be there, "I was down there for forty years, do you really want to know what comes next?"

"Yeah, Dean..."

He turned his head slightly, looking at him, "Don't pity me, don't you dare. Ten years later I broke, I stepped off the rack, I went with Alastair willingly. No more pain, no more torment. Stepping off that rack was the hardest yet most fulfilling thing I've ever done. He taught me, trained me, to be like him. I was his apprentice for ten years before Castiel came for me. If he had been just a little later I might not be here, I might be one of those black eyed bastards. So don't you dare pity me."

"I can still be sorry that you had to go through that."

"One good thing came out of it, I got Ruby to talk in less than two hours." He finally looked over at him. Well, his brother was certainly good at looking like a kicked puppy, "Sammy, everything is going to be fine. Do you feel better knowing?"

"Yeah, I do." He paused, looking out the windshield, "Where's Lilith?"

"Couple towns over, looks like following demon signs payed off." He continued down the highway, "Are you ready for this? She's going to want you to kill her, you're going to have to go in first, draw her out, do whatever it takes to pin her down and get that symbol carved into her."

"I know, I'll take care of it. She's not going to go down easily if she finds out we're not going to kill her."

The rest of the drive was in silence. Dean couldn't stop thinking about Hell. Would Alastair try to break him the old fashioned way? Would he use torture or compassion? Not that his comfort ever came from a place of compassion. He shook his head, no, think about the task at hand, they were going to kill Lilith and he was going to go find a nice carefree life away from monsters and demons, just so he could make Alastair wait that much longer.

She was in an old church in Wyoming, waiting for them. They had to make this look good, Ruby wouldn't have been able to get in contact with her. It was going to take time for Ruby to be able to communicate with anyone. Sam went in first while Dean waited just outside. He knew Sam would get the job done, they were coming down the home stretch.

 

-Sam-

 

The moment he stepped inside Lilith smiled at him, "Sam, it's so good to see you."

"Lilith." At least she wasn't in a child's body, "I'm here to take you out." He adjusted the blade in his hand.

She spread her arms, "Come and get me, I've been waiting for you." Sam was on her in an instant, carving the binding sigil into her chest, "What?" She shouted, eyes going wide as he pinned her in place.

He could feel Dean's presence coming into the room, moving swiftly, "Yeah, sorry, not going to kill you, just going to cut you up a little bit and bury you where no one will ever find you again." Dean grinned down at her.

The brothers set to work, Dean taking the first swing. It took a couple strikes to remove an arm but honestly, he was ok with that. Sam worked just as fast and if he denied that he didn't find this satisfying he'd be lying.

"Lilith, this is the point where we say good bye." Sam stood over her, looking down, he wanted the last swing, wanted to cut her head from her body, "I can't say it's been fun but I'm happy to say, you lose." He swung, the blade slicing through.

Dean clapped a hand on his shoulder, "Let's get these bits buried."

 


	5. Chapter 5

-Dean-

 

Things had settled down a little after they had distributed her remains to the four corners of the world. Ok, so they really just buried her in cement, each piece in a different state. Now they were relaxing and Dean was wondering how he could bring up early retirement. He kept putting it off, Sam was so happy, there was no way he was going to be the one to ruin it.

"Dean, what's up?"

The river they had stopped at was nice, the beer was better though, "What? I'm thinking about grabbing us a couple fishing poles."

Sam shook his head, smiling, "Yeah, no, let's just enjoy our vacation, deal?"

"Yeah, deal, get me another beer, Sammy."

It only took two weeks for him to forget about his deal. They had been on a few hunts, vampires and a ghost, things were picking up again, keeping them occupied. They were tracking down a demon in Colorado. Ok, so it was a couple of demons in Colorado. They had tracked them to a small house on the outskirts of town. Hopefully they could get a drop on them.

He motioned to Sam, Dean would go in the back while Sam took the front. He slid around the side of the house, eyes darting around before heading for the back door. Looking back he couldn't be sure what he had missed but the last thing he recalled was his hand reaching for the door and then there was a sharp pain in his neck, a crack, then nothing.

Dean's eyes opened to heat and fire and pain. He sighed softly, hanging in his hooks, waiting. Hell, the deal, he had forgotten but this was a rather painful reminder of just what he had gotten himself into. There was no calling for Sam this time, no begging, he knew what was going to happen, Alastair would show up for him eventually. He was thankful he didn't have to wait long, Alastair's arms were familiar as they wrapped around him, removing the hooks and chains, carrying him back to the familiar workroom and the very familiar rack.

"Good morning, Dean, is it Monday already?" Alastair chuckled softly as he settled him into place, "Bright and early, so good to see you again. Do you know how much I've missed you? Ten years my dear boy. How would you like to begin?"

He closed his eyes, thumping his head back on the rack, "Good morning, Alastair."

"Polite, good, but we can do better. Who am I to you?"

Deep breath, "My master." and let it out.

He smiled, stroking his fingers slowly down his cheek, "I'm so very pleased to have you back. You never should have left, that winged rat should never have taken you from me." His fingers dug into his cheeks for a moment before letting him go, "We're going to have to start from scratch, aren't we, Deano?"

 

-Sam-

 

Dean was gone. He had killed each of the demons in that house, taken them all out before finding Dean's body. Death finally caught up with them, it was bound to happen, Sam just thought he would have more time or they'd go out together. It had to stop, he had gone to Bobby first, no more hunting. Dean's body was heavy in his arms as he stood on Bobby's doorstep, waiting for the old hunter.

"Sam..."

He looked up, meeting his eyes, "Bobby, please, we need to bury him. I-I don't know what to do."

He laid a hand on his shoulder, "You want him to stay here?"

Sam nodded, tears in his eyes, "It was a stupid hunt, just shouldn't have happened."

Bobby squeezed, pulling him inside, "Lay him on the couch, let me get you a drink and we'll find a good spot so we can visit him, ok?"

They buried him out back, gave him a better marker this time. He needed to let go but he wanted his brother back, whatever the cost. He couldn't tell Bobby, couldn't let him know he was going to try to make a deal. Two days he spent in a bottle on Bobby's couch before going out and finding a crossroads.

"Sam Winchester." The demon who showed up was short and English, "Crowley, King of the Crossroads, what can I do for you?"

"I warrant the royal treatment? I want my brother back."

He shook his head, "That's a little out of my reach. Can't bring him back, not even for your soul. Going to have to just let him go, was his time and all." He slid his hands into the pockets of his fancy tailored suit, "Is there something else I can interest you in? A good life? Forgetting you ever had a brother, that you're a hunter?"

"No." He shook his head, "Is he in Heaven?"

"Yes." He didn't look happy about it.

A wave of relief passed over him, "Good, good." He turned and walked away, heading back to the Impala.

"Sam," Crowley looked him in the eyes when he turned, "take a break." He snapped his fingers, disappearing.

He was actually going to take his advice, was going to take that break, and maybe learn to live without his brother. He spent two months on the road, taking odd jobs, trying to find his niche. It was then that he met her, Aubry. She worked as a barista at a local coffee shop. She was made of fire, all energy and sunshine. She made his mornings that much brighter.

He smiled weakly at her over the counter, had never worked up the guts to get her number, "Hi, Aubry."

She smiled, "Sam, want your usual?" She already had it made up, "It's on me, you look a little sad today."

"Thanks." He headed for the door before stopping, "Thanks, Aubry."

As he left to find his job for the day he noticed a number scrawled across the cup. She had taken the first step, given him her number. It was the two month anniversary of Dean's death but maybe today would be different. Maybe she could bring a little light into his world, maybe he could tell her everything, maybe she would understand, he just needed to take a leap of faith. He stared at her number, Dean would call her, Dean would convince him to call her. He ran his thumb over it, he would do it, he'd take that risk.

 

-Dean-

 

He ached, how long had it been since he had returned to Hell? Alastair wasn't keen on telling him how long he had been strapped to the rack. It had to be days, weeks, months even. Every morning it was the same, good morning Dean, good morning master. He wouldn't refer to him as anything else, that had been carved into him on day one. Alastair walked into his workroom, blade spinning between his fingers. He held the form of the last meatsuit they had met in, white eyes gazed out at him, a smile on his lips.

"How long?" Dean swallowed, clearing his throat, "How long have I been here?"

The demon tapped the blade to his lips, "Twenty years now, yes, to the day."

Dean closed his eyes, hanging limp in his shackles, "You haven't even given me the offer, not once." He would take it, in a heartbeat, he would have taken it on day one.

He chuckled softly, "Mmm, Deano, that's not how it works this time. We don't need the Righteous Man to shed blood in Hell, that's come and gone. No deals to be struck this time." He looked thoughtful, tapping the blade to his lips.

The cuffs bit into his wrists as he lunged forward, "Then what did you want me here for? Just to get your rocks off torturing me?"

"Perhaps an exception can be made. Do you want to come off the rack, lay the knife into others, break them to pieces?" He pressed close so they were barely touching, the demon clothed, the human naked, "Do you want to be my apprentice again? My soul to twist and mold as I see fit?" Their lips were almost touching, "Tell me, what is it that you want?"

"You carved me into a new animal, you made me, don't you want to set me loose again? See exactly what fifty years of torture have made me into? Aren't I your greatest success story? The Righteous Man, little Deano broke in thirty." He sneered, glaring at him, "Aren't I worth a deal or two?"

He patted his cheek, "You're worth every deal." He chucked softly, "What do I get? If I let you off, what are you giving me in return?"

A soft growl escaped his lips, "You get me. You get me back, you wanted me, now you have me, what's the hold up?" He paused, "How'd you do it? No way should I have died so soon."

"Crowley read our little contract, he just can't keep his mouth shut. I'm sure he offered some big prize to the winner."

"And you kept your hands clean." He sighed, bowing his head, "Do whatever you want, you have what you want, if you want me strapped to the rack forever, then that's your decision. So pick, let me loose or cut me up."

The demon closed the distance, biting and licking at his lips, "Open up, Deano, let's see what kind of animal you've become." Dean's mouth filled with blood, Alastair's blood. He swallowed it down, moaning against his lips, chasing them when he pulled away. The demon smiled, grasping his chin and tipping his head up, "Open those peepers, let me see."

His eyes slipped open and Alastair's smile grew, "All that pretty green being swallowed up by black." His thumb brushed beneath each of them, "Alright Dean, let's get you back on track. You're a little behind, all that time spent topside with the angel's grubby little paws on you." He snapped his fingers and the shackles released, dropping Dean to the ground, "You know the rules or do you need a refresher?"

"No, master, I remember the rules." He fell to his hands and knees, looking at the ground.

Long fingers stroked through his hair, "Good boy. Shall we begin? I think I want some personal time with my little pet."

 

-Alastair-

 

His rooms were connected to his place of work, he enjoyed hearing the pleading and crying of his latest project. Now, now he had Dean, and the past twenty years had been filled with the sounds of his favorite as he danced to the tune of his blade. Dean crawled at his feet, the perfect place for the human. As he changed he wouldn't be crawling like a dog any longer, he would earn the right to walk beside him. His boy would always please him, there was no question in his mind that Dean would do everything perfectly, it would just require a little work.

He motioned to the bed, waiting for Dean to show him exactly what he remembered. His boy crawled up, settling onto position, his hips raised, chest and face pressed to the mattress. Dean hadn't given up, quite the contrary, he just didn't want to go back on the rack. Alastair knew that for the moment he would be a good boy and he was prepared to enjoy it while it lasted.

"Shall I prepare you this time? Open you up before filling you?" His fingers ran over the swell of his ass, feeling his skin twitch beneath his fingers, "Or shall I take you dry, leave you walking funny for weeks."

Dean's fingers clenched in blood red sheets, "Do you want an answer or are you just messing with me?"

"Enlighten me, Deano. How should this play out?" His fingers dipped down to run over his hole.

"I'd rather be prepared."

He tapped over it slowly, watching as it clenched and unclenched, "Hmm, just this once." Slick fingers pressed forward, finding their way inside. His boy gasped so prettily, "You're lucky, it isn't every day someone gets to hop off the rack. It usually takes a few hundred years to fully turn someone into a demon. You're special." He twisted his fingers, pressing against his spot. "Then again, this isn't your first time here. I think we made a breakthrough with you. Break them down, let them up to torture others. Forty years and you were almost fully a demon." Dean let out a cry as Alastair's fingers pressed hard against his spot, a third one pressing in to stretch him, "How long will it take this time? Twenty years on the rack and your eyes were already darkening. You must have some fond memories."

"Master, please." Dean's voice was a low growl, "Come on, don't tease me."

He shook his head, retrieving his fingers before freeing himself, leaving his clothes on. It was a sign of dominance as he pinned Dean with one hand on the back of his neck before sinking into him, filling him completely.

"Let me hear you scream." He snapped forward, starting a brutal pace, wanting to hear every sound that came from his boy's lips.

Dean bucked beneath him, moaning and crying out, losing himself completely in the act. When his boy let loose he was a wild thing, more animal than man. It didn't matter what he was doing, in this state he let himself be known. There was no doubt in Alastair's mind that he was enjoying it. They moved together, letting go, the demon biting and nipping at whatever he could reach, nails dragging down his sides.

"Close, fuck!" Dean howled, his fingers gripping and tugging at the sheets.

Alastair snarled, "Not until I say."

A low whine escaped him, one hand reaching down and grasping firmly around the base of his length, squeezing hard to stave off his release. This earned him a soft kiss in reward as those hips snapped forward, driving himself in as deep as he could. His boy was reduced to begging, the sounds flowed from his lips like water, as he fought not to come. He would suffer for it if he disobeyed but he was such a good boy, he could do this. The demon laid a kiss on the back of his neck, his lips sliding forward to his ear.

"Dean, come for me." He bit the lobe sharply as he snapped forward hard. Dean howled, letting himself go, clenching and spasming around him, drawing forth his own orgasm, "Heaven..."

"Master." He moaned softly, falling limp, gasping for breath.

Alastair laid over his back, forming himself to his body, before rolling them to the side, "Such a good boy for me." He praised, "Rest, we'll play again soon." He had just the thing in mind, Dean needed to get back to his old job, needed to start cutting again. Those pretty eyes of his needed to finish turning, his animal needed to be unleashed, "Mmmm, relax Deano. Good boy."


	6. Chapter 6

-Dean-

 

            He ached, his body throbbed, but Alastair's weight was comforting against his back. He was off the rack. A slow breath escaped his lips, he was off the rack. It felt amazing to finally be free and although his body hurt it was a relief. The room was just as he remembered, sparse but comfortable, although he still thought the decor sucked. Jars full of body parts and odd objects lined the walls, Dean hadn't been too keen on it the first time, and this time was no different. The demon was still asleep, leaving Dean to figure out what he could do without waking him up. His master was a notoriously light sleeper and didn't like being disturbed. The first time he stepped off the rack it had taken years to figure out a way to not wake the demon, this time he was pretty sure he could manage to escape. He slowly slid down, Alastair's arms sliding off him as he rolled off the edge of the bed. Years of practice allowed him to land silently. He needed something special to get into his master's good graces, needed something that would please the demon.

            He slid into the workroom, looking around for a moment. The rack was unfortunately unoccupied since he stepped off. He ran his fingers over it slowly, thinking about what he was going to do for his master. Then the thought hit him, he would create a symphony for his master to wake up to. He slid outside, closing the door softly as he moved to collect a soul. It had to be perfect, he chose a young woman, so very much like his first victim. She was babbling and sobbing as he removed the hooks, his fingers slid through her hair as he made soft shushing noises, it wouldn't do to wake Alastair up too soon.

            "It's alright, I'm here to help you." It was the only way to quiet a soul in Hell, false hope. Part of him hated it but that part was slowly being swallowed up by darkness, by the demonic force that was growing inside him, "Shh, no more tears. You have to be quiet for me, if you're not someone is going to take you from me and you'll be back hanging from hooks." She fell silent and he smiled, "There." He carried her gently back to the workroom, gagging her before strapping her down to the rack. Her eyes went wide and she began to struggle, muffled sounds escaping her lips, "Sorry, I had to keep you quiet." He patted her cheek, "At least until I was ready to make you sing."

            He wrapped his fingers around Alastair's favorite silver razor. She struggled harder, trying to scream as the blade came closer. Slowly he went to work, beginning to cut. She squealed behind the gag, tears streaming down her cheeks.

            "What was that? Sorry, I can't hear you." He removed the gag and she screamed, a loud sob escaping her lips, "You were trying to tell me something, well, spit it out."

            "Please, stop!" She sobbed and he cut.

            "Mm, what's the ruckus?" Alastair's voice was rough with sleep as he stepped into the workroom.

            "Good morning, master." He slid the blade down her side wringing another shriek from her lips, "I thought you would enjoy a symphony to wake up to."

            The demon came up behind him, wrapping his arms around him slowly, "Mm, I do. Such a good boy you are." He laid a soft kiss behind his ear, "I'm pleased you haven't forgotten your training. I would hate to have to start back at square one. You always were such a quick learner."

            "Thank you, master." He continued to cut, his hands turning scarlet with blood, "I aim to please." He grinned, tipping his head and nipping his shoulder.

            "Naughty boy, you would dare lie to me? Hm? I know you don't, aim to please, as you put it. You have more fun being difficult."

            He flayed the skin from her arm, pulling it off in strips, "Of course I do, master, just for you." She screamed as another swath of flesh was removed, "Besides, if I don't please you I'll be having the skin from my back removed. See, fast learner."

            Alastair shook his head, his fingers sliding down his sides, "I want to take you topside some day soon." He licked up his throat slowly, nipping his ear softly before tugging on it, "Want to set you loose after those pretty eyes of yours turn black." He growled softly, "Keep working, the sooner you turn, the sooner I can let you loose."

            He froze, his blade hovering over the woman's shoulder, "You want me to go topside?"

            "Yes, I want to set you loose, watch you play." He gripped his hips tightly, his fingers leaving bruising marks, "I can't wait to see you when you've finished turning. What kind of animal you'll truly become." Teeth dug into Dean's shoulder, "Are you having second thoughts about stepping off the rack?"

            Dean gasped, squirming, he blade sliding down into her flesh, wringing a scream from her lips, "No, never, no second thoughts." He didn't want to be strung back up but if he was taken topside he ran the risk of Sam seeing him.

            "Then what's the problem? What has you all uptight and nervous?" He growled into his shoulder, biting again, hard enough to draw blood.

            "Sam." The name came out choked.

 

-Alastair-

 

            Sam, Sam, it was always Sam. He needed to carve that out of him, he thought he had, but apparently he hadn't made the impact necessary. He shook his head, running his tongue over the wound he had left in his shoulder. What was he going to do with his poor apprentice? This couldn't be allowed to stand, perhaps Dean needed some motivation. The bitch was sobbing and Dean had stopped cutting, still frozen at the thought of his brother.

            "Dean, down." The reaction was automatic, he fell to his hands and knees, bowing his head, "Hm, I thought we were past this. Why do you think I let you off the rack?"

            "My winning smile?"

            He shook his head, giving his ass a hard swat, "Because you belong to me and after another twenty years on the rack I believed we were past any thoughts of little Sammy."

            "It would ruin him if he saw me as a demon, if he knew I wasn't in Heaven."

            He reached down, grasping his hair, tugging at it lightly, "Who says that we have to be anywhere he is? The world is bigger than the U.S., who says when we go topside that it has to be anywhere little Sammy can find you, Deano?" He paused, tugging his hair again, "Or are you worried that the moment we go topside Sam will somehow know?" He paused, once Dean had turned fully he wouldn't care about what Sam thought, he wouldn't care about his brother at all. The issue at hand was that Dean would resist as long as he thought going topside would happen the moment he turned, "Perhaps we can discuss this. If after you turn you desire to stay here maybe we can make that happen."

            Dean stared at the ground, "I won't hurt Sam."

            Alastair rolled his eyes, "I don't care about your brother but you're going back on the rack. So sorry my boy, your behavior leaves a lot to be desired. Although you gifted me with this wonderful symphony you questioned my decision, my wishes, you know how I feel about that."

            He swallowed hard, "I'm sorry master, please, I don't want to go back on the rack."

            "Is that your choice?" He growled, jerking his head back hard so he was forced to look at him, "Tell me, Dean, who makes the decisions in this relationship?"

            "You do, master." He choked back a moan.

            He released his hair, stroking trough it gently, "Good boy, perhaps I won't have to strap you back in."

            "Whatever pleases you." He said softly and Alastair felt immensely pleased by his words.

            He smiled down at him, "Good boy, just what I wanted to hear." He paused, "Get back to work, no more hesitation or I will have to reconsider letting you off the rack so soon."

            Dean nodded, getting to his feet and kissing him softly before turning back to the woman. He smiled at her, "Back to the grindstone."

 

-Sam-

 

            It had been six years since Dean had died and he had met Aubry. Under her urging he had gone back to school, gotten his law degree, and now he was going to take the next step. He was going to ask her to marry him. He was nervous, had never thought he would get this far, that his future would become so mundane. Again he found himself staring at the ring, watching it sparkle in the light. It had taken him a bit to save up and now it was time.

            He was sitting on the couch in their little San Diego apartment, waiting for Aubry to get home from work. He turned the box in his fingers nervously, his eyes locked on the door. She would be home any minute and each minute that passed was one too long.

            He could hear the keys in the lock and immediately perked up, "Sam, I'm home!" Almost immediately he was down on one knee, looking up as she opened the door. She stopped mid-step, blinking down at him, "Sam, what're you doing on the floor?"

            "I had something I wanted to ask you." He rubbed the back of his neck, looking nervous, "Aubry, you know I love you, like always and forever love you, and I want to ask, will you marry me?"

            She blinked down at him before a smile slid across her face, "Why, Sam Winchester, I thought you'd never ask." The grin that spread across his face was one of pure joy. He was on his feet in a flash, wrapping his arms around her and scooping her up, spinning her around. She laughed, clinging to him, "Hey, where's my ring?"

            "Oh!" He out her down, scrambling to get the small velvety box out, holding it out to her, "Here!" He pulled it out when she held her hand out for him to put it on.

            She leaned forward, kissing him softly, her fingers carding through his hair, "We should celebrate."

            "Damn right we should!" He grinned, spinning her around again, "Where do you want to go? What do you want to do?"

            "Drinks, you can go to work hungover a little, they'll understand!"

            He shook his head and smiled, "Sure they will. Ok, let's go."

            This was the happiest Sam had been in a long time. He sat watching as his fiancée danced, trying to get him to join in. He shook his head but finally relented, letting her pull him up and onto the dance floor. He was horrible at this but he had to admit he was having fun. They made it home after a few hours, drunk and laughing as they fell into bed. It was rough, wild, and Sam fell asleep with his arms full of his auburn haired fiancée.

 

-Dean-

 

            Seven hundred and twenty years and he was starting another day of work. His tools were laid out and polished and the soul on the rack was fresh, untouched. Every day was the same, he rolled out of bed, kissed Alastair, and the two of them went to work. Most days he was allowed to work alone but every now and then Alastair would follow him into his workroom and watch. Seven hundred and twenty years of Alastair standing over his shoulder, of the elder demon looking at his eyes every moment he could. He wasn't sure why he had to check every time they saw each other, it was getting annoying.

            He felt the demon before he saw him, the white eyed inquisitor's fingers slid down his sides, fingers digging into his flesh, "Good morning, Dean."

            He sighed and closed his eyes, "Good morning, master."

            "Let me see." Those fingers slid along his jaw, grasping his chin and turning his head.

            He snapped his eyes closed, "Not until you tell me why you're so obsessed with looking at my eyes."

            "Every day they get a little darker, I'm waiting for that moment when those peepers of yours become pitch black. Let that pretty little demon loose." He growled lowly, his fingers tightening on his chin, "Now, open them."

            A sigh escaped his lips, he didn't feel any different but Dean had no choice. He opened his eyes, "Feel better?"

            Alastair's lips crashed into his nipping and sucking at them, "Mine, my demon." Dean let out a grunt of surprise, stumbling back into the rack. Alastair pulled back, licking his lips softly, "Good boy, my good boy." He chuckled softly, "Mm, you are perfect, have I told you that before, Deano?"

            He felt a little confused, if his eyes were black why didn't he feel any different? He blinked at him, "Why don't I feel any different?"

            The elder demon chuckled softly, "Because we haven't set you free." He leaned forward, chuckling in his ear, "You've turned but we haven't let you loose." He tugged his ear, "We have to unleash the beast, so to speak. Well, it's quite literal. It's like a coiled spring, waiting deep inside you, waiting for me to let it loose."

            Dean froze, "How are you going to let it loose?" He didn't want to be cut to pieces again, it was so much better on this side of the knife, but if it was a necessity, well. How could he argue?

            "In the best way possible."

            The kiss surprised him, soft and gentle, completely different than he was used to. Alastair had kisses that seared deep, left their mark indelibly on a person's soul, and yet, this was somehow even more. He could feel it deep inside, coaxing and cajoling, urging him to relax and just let himself go. A soft moan escaped his lips as he was pressed against the soul bound to his rack. He let himself go, lost himself in the sensation of lips upon his own, of fingers dragging through his hair, and the press of bodies. The soul behind him was yelling, struggling in the metal shackles and hooks that kept him firmly in place. Dean ignored him, his eyes closing and lips parting as the kiss was deepened. It felt like Alastair was reaching deep inside him as he was turned, the clatter of his tools hitting the ground causing him to pull back from the kiss as he was forced onto the table.

            "Hey! Was that..." He was silenced by demanding lips.

            "Shut up, Dean." He growled, rocking their hips together, his fingers gripping his hips tightly, "I'm going to fill you up, make you scream, and pull your true self free." He hissed into his ear, pressing down against the naked ex-hunter.

            Dean moaned, spreading his legs and rocking up against him, "Please." He would gladly beg if it would get him to go any faster.

            Alastair shook his head, his hands sliding over his hips, "Spread yourself open for me, I want to watch as you stretch yourself, get you ready to take me deep inside." Dean let his head thump back on the table, his fingers immediately going for his hole only to be stopped by a firm grip around his wrist, "Suck them first, boy."

            He shuddered but did as he was told, sucking is fingers until they were wet before bringing them back to his hole and pressing in. He arched back, gasping softly as he pressed into himself. He worked fast, barely giving himself enough time to adjust before adding a second, then a third, working himself open with quick thrusts and rotations.

            "Please! Dammit, I'm open enough, just do it." He jerked his fingers free, glaring up at him, "If you don't I'm going to pin you down and ride you."

            Alastair chuckled softly, snapping his fingers, binding him firmly to the table, "Oh, you will, will you?" He leaned down and kissed him slowly, his tip nudging at his hole, "Don't worry, I'll fill you up just as you should be." He pushed forward, sliding in fully with one thrust, "Isn't that better?" He licked his lips, nibbling at them before beginning to move.

            Dean moaned, tipping his head back, eyes fluttering closed. He couldn't move, he had to just lay there and loose himself in the sensations that Alastair inflicted upon him. His voice raised in pleasure, howling and keening as he was filled and emptied with each thrust. His cock dripped steadily, a puddle forming on his stomach as another gasp was punched out of him by another hard thrust.

            "How does it feel?" He bit at his lips harshly, "Let me hear it."

            "Fuck! Alastair!" He moaned loudly as his spot was smashed into, "It's too much! Feels too good, please, I need to come!" He arched against the invisible bonds holding him, his hole clenching over the white eyed demon, "Please, please, dammit!" He wasn't above begging, not when he couldn't move, couldn't touch himself, couldn't thrust back to meet Alastair's movements, "Touch me, faster, harder, own me!" He growled, bearing his throat to him.

            The demon growled, "Tell me how you feel inside." He ordered, grunting as he started moving faster.

            He jerked, moaning loudly, it felt like something was tearing free, ripping through him, "It feels wrong! Something jerking, tearing!"

            Alastair grinned, "Good." He slammed into him, hitting his spot hard.

            Dean howled, jerking back and coming hard, feeling that part of him tear free. He spasmed, clenching tightly over him and pulling Alastair over the edge. He moaned, going limp, his body twitching slightly in aftershocks. Fingers slid over his face, stroking under his eyes softly.

            "Fuck." Dean groaned, tipping his head into his hands.

            "Open your eyes." He ordered.

            Dean grumbled, opening his eyes slowly. Black met white and the new demon grinned, leaning up and biting his ear sharply, "Don't order me around." He growled.

            Alastair snarled, "How do you feel?" For the moment he ignored the bite.

            "Free." He moved from his ear to his lips, biting and nipping at them.

            "You're mine." He growled lowly before driving his teeth into his throat, biting hard, drawing blood, "Now behave." He pulled back and out, leaving him limp and sated on his tool table.

            "When do I ever not behave?" He pushed himself up, looking at the other demon.

            "Whenever you think you can." He walked away, leaving Dean to clean up and get back to work.

 

-Alastair-

 

            He gave Dean five earth years to get used to being a demon before broaching the subject of going back topside. Dean was perfect, his perfect demon, and it was about time to let him loose up top. Dean was working, splattered with blood as he stood before his rack. The white eyed demon came up behind him, pressing against his back, wrapping his arms around him slowly.

            "Good evening, Deano, how's work been going?"

            He leaned back into him, twirling the blade between his fingers, "He's boring me, we don't get anyone fun anymore. The crossroads demons are shirking their duties. They need to go after a better caliber of souls."

            Alastair slid his hands up his sides, smearing the blood across his skin, "I was thinking we could take a little trip, head up to the freezer, let you loose up top."

            Dean cocked his head to the side, visibly thinking for a moment before grinning, "Sure, let's take a little trip, I wonder how Sammy's doing."

            "Well, let's find out."

 

-Dean-

 

            It was odd to be in a body, maybe it would have been different if it had been his own but it was rotting in the ground, so he had hopped into a twenty something man walking down the streets of California. He smiled, looking down at his hands as he flexed his stolen fingers.  The original owner of the body was screaming and Dean couldn't help but laugh. The feeling of walking around topside was different, he never realized how cold it was, ninety degree weather and he thought it was cold, he shook his head and stretched. Alastair should be around somewhere but he was more looking forward to finding Sam than spending time with his master. His brother was supposed to be living in San Diego, or at least that's what he had been told, it was only a matter of finding him. He patted himself down, feeling for a cell phone, the guy had to have one. A grin spread across his face as he pulled it out, sliding his thumb across. The guy didn't even bother to lock it, he rolled his eyes, security these days. A search for Sam Winchester actually netted him results. Samuel Winchester, attorney at law, his baby brother was a defense attorney. He wasn't too far from his office either, it was time to pay him a visit.

            He shoved the door open, grinning as he strode past the receptionist. She was on her feet in a moment, going after him quickly, "Sir! You can't go in there, you need an appointment!"

            He turned to face her, grinning as she almost ran into him. She was a pretty little thing, all petite with auburn hair, she had spunk, "I do, do I? What if I told you that Sam Winchester is my brother? Would I still need an appointment?"

            She scowled at him, putting herself between him and Sam's office, "I would say you're an asshole and an idiot, Sam's brother is dead, so yes, you need an appointment."

            He pressed forward, trying to drive her back but she held her ground, "You're a little spitfire, aren't you?"

            She pressed back, "I've heard it before, now leave before I call security."

            "Aubry? What's going on?" Sam stepped out of his office.

            He grinned at him over the top of her head, "Heya, Sammy."

 

-Sam-

 

            He froze hearing those words. He didn't know the voice but those words, he thought he would never hear them again. The words, the inflection, that smile, was purely Dean. He couldn't move, couldn't speak, as he stared at this unknown man who acted and sounded like his brother, his dead brother. Aubry was between them, looking throughly confused.

            "Sam? Are you alright?" She moved over to him, her fingers falling onto his shoulders, moving up to cup his face, "Sam, talk to me."

            Her touch snapped him out of it and he shoved her behind him, "Dean." His voice was flat, eyes narrowed as he shielded his wife.

            Dean's smile grew, "I didn't think you'd recognize me! I should have known my baby bro was too smart to be fooled by appearances." He paused for a moment, "Who's the pretty red head? You hired one hot little secretary."

            "My wife." It wouldn't do any good to lie to him, "How are you here? You were supposed to be in Heaven."

            Dean's fingers slid over Aubry's desk, picking up papers absently, "You got married? Never thought I'd see the day!" He hopped onto the polished surface, "As for me and Heaven, well, it just didn't work out. You remember Alastair and what he did to me, well, at least what I let you know. See, he fucked me, made me beg for it, and the only way I was going to get release was for him to get my soul. When that demon snapped my neck I woke up downstairs. Can't say I'm complaining, it's cold up here, practically arctic. It took awhile but damn, I feel so much better. Alastair's awesome in bed by the way, just damn, nothing compares to being bent over his work table and pounded into oblivion." His eyes flashed black and Sam felt a chill rush down his spine.

            "You're a demon." He couldn't keep the waver out of his voice, "What are you going to do now?"

            He kept Ruby's knife strapped to his ankle, old habits die hard after all, but he wasn't sure if he could do it. It may not look like Dean but it was definitely his brother in that body.

            "I'm not sure, got a pass topside and figured I'd come for a little family reunion, see how baby brother's doin'. Big shot attorney, got a nice office, sexy wife, isn't she a little short for you by the way? Bet she fits nicely under your chin when you cuddle, you do cuddle, don't you? She looks like a cuddler and you're like a big teddy bear. I heard Crowley call you a moose one day after he went and visited you." He shook his head, "Trying to make a deal, for shame, that's my job." He paused, his smile growing wider, "Wanna make a deal?"

            Sam knew he was trying to get a rise out of him but he couldn't stop himself from responding, "Fuck you, Dean." His hands clenched into fists, "Knowing that you were in Heaven kept me going after you died. No one would deal with me, Bobby, Aubry, they pulled me back and I moved on." He swallowed hard, unable to stop the next words out of his mouth, "You should have stayed dead." The words were hollow, he felt like part of himself had been ripped free, dug up from where he had buried it years ago.

            His brother, no, the demon, gasped, putting a hand on his chest, looking offended for a brief moment before snickering, "You cut deep, little bro, words hurt ya know." He hopped off the desk, "What if I want to mess around a bit, have a good old fashioned fight? Knock down, drag out, you do remember how to throw a punch, don't you or has being a lawyer made you soft?" His fingers twitched and the letter opener from Aubry's desk flew into his waiting hand, "Come on, Sammy! Make this fun for me or do I need to give you some incentive?"

            No, no, demons would use whatever they could, had no care about who they hurt. In fact, most enjoyed hurting people. Sam couldn't let Aubry be hurt because of something from his past. He had told her about demons, about vampires and werewolves. She had taken it all in stride but had never faced anything, never seen one of the creatures that Sam and Dean used to hunt. He moved quickly, shoving her back into his office and closing the door before grabbing the blade from its sheath.

            "I won't let you hurt her." Aubry was family and he would die to protect her, "Dean, come on man, don't do this. Just leave us be." He needed the right moment, the right distraction, he needed to exorcise his brother.

 

-Dean-

 

            Sam looked amazingly conflicted, Sam had recognized him almost immediately and didn't that bring a spark of, something, to his dead heart. He should have known his little brother was smart, that he hadn't given up hunting completely. He wondered if he had hidden any devil's traps anywhere but part of him really didn't want to find out. His eyes flicked to the blade in his hand, that would definitely hurt and maybe even kill him, now wasn't that a cheery thought? He held the letter opener firmly, grinning at him.

            "Ready Sammy? It takes two to tango."

            Little Sammy looked resigned as he fell into an easy defensive stance, Dean grinned at him before making the first move. He darted forward, watching as Sam dodged out of the way, the letter opener slashed across the arm of his suit.

            "Damn, Sam, you give your wife a knife? Damn thing is sharp, cut right through your coat."

            "Dean, you don't have to do this. You're still my brother!"

            He dodged back again and Dean snarled softly, "Come on, fight back! It's no fun this way."

            Sam shook his head, moving back with each swing of Dean's blade. The demon scowled, what was he doing? He drove him back, stepping through another door, or at least he tried to, he impacted with the invisible field of a devil's trap. The sigh that escaped his lips was long and drawn out, he should have known Sam would always be prepared whether he left hunting or not.

            A sigh escaped his lips, "What're you planning now?" He leaned against the wall, "Going to stab me? Kill me? Are you gonna send me back downstairs because I have to tell you, I'll be back eventually."

            "I'm not going to kill you but you're going to leave us alone. You're going to either smoke out or I'm going to exorcise you." Sam's voice was raw and hollow, laced with pain, "I'm going to go back to my wife, back to our life, and you will never come after us again or I will kill you. Am I clear?"

            "You couldn't be clearer but I'm not going to leave this body, it's fun up here. Do you realize how long it's been since crack, bam, back in Hell? 840 years." He crossed his arms over his chest, "So, yeah, not going to smoke out."

 

-Sam-

 

            He closed his eyes, keeping himself steady, he couldn't hurt his brother, couldn't even bring himself to exorcise him. Wasn't that a kick in the ass? He wasn't sure what he was going to do. He wouldn't set him free but he couldn't stay in his office until he got bored either. 840 years, he was sure to have developed a little patience. Part of him was elated to see his brother again and the rest was petrified by the kind of damage he could do.

            "I don't want to do this, please, Dean, don't make me." He was pleading, he knew he was, but it was the only thing he could do, "I don't want to hurt you, don't want to kill you, just go." He was on the verge of tears but he couldn't let them loose, couldn't let them free, "Just smoke out and leave me alone."

            "Poor little Sammy gonna cry?" He snorted, "When did you become so soft?"

            Aubry stepped out of his office, head held high, glaring at the demon. Dean was immediately taken aback by the much shorter woman, "You're not Sam's brother. You are not the man he's told me about. He idolized his brother, the good man, the hunter, the protector and provider, you're nothing but a shadow, a pale comparison." She stepped to the edge of the trap, "Even though you are nothing but a shade he still cares about you. He won't kill you, doesn't even want to hurt you, and I'm not sure he can even say the words needed to send you back to Hell where you belong." She paused, green eyes locked to green, "But I can and I will. Exorcizamus te, omnis immundus spiritus, omnis satanica potestas, omnis incursio infernalis adversarii,omnis legio, omnis congregatio et secta diabolica."

            Dean was grunting softly, his nails digging into his palms as he hit the floor. Sam jerked forward, barely stopping himself at the edge of the trap, "Aubry, stop!" He couldn't stand it, seeing his brother in pain, "Enough."

            She stopped immediately, "Sam, he can't stay here. We can't just let him go, what do you think he'll do?"

            "It's hurting him." The excuse was lame even to his ears.

            The demon pushed himself up, letting out a soft grunt, "You've got guts girl." He pushed against the trap, "I should gut you, see what makes you tick." He turned to look at Sam.

            This thing wasn't his brother, not to say something like that, but deep in his heart he knew that was a lie, his brother was a demon. He looked at Aubry, "I'll do it." His gaze went back to Dean, "If you come back to harm me or my family I will do whatever I have to in order to keep them safe. I can't let you go so that leaves only one choice." He took in a shaky breath, "Goodbye Dean." His voice broke and it took a minute to get himself back under control.

            "This isn't the last you'll see of me, I promise you that." He growled, eyes black, "See ya later Sammy."

            "Exorcizamus te, omnis immundus spiritus, omnis satanica potestas, omnis incursio infernalis adversarii,omnis legio, omnis congregatio et secta diabolica. Ergo, draco maledicte. Ecclesiam tuam securi tibi facias libertate servire,te rogamus, audi nos." He barely made it through the exorcism before the tears began to flow.

            He fell to his knees, staring at the ground as Aubry rushed over to him, hopping over the recently vacated body. Warm arms wrapped around him, drawing his head to rest on her chest as he began to cry. He clung to her, sobbing into her shirt. His brother was a demon. All the goodness and light had been cut out of him and all that was left was dark and primal. Her fingers stroked through his hair as she softly began to sing, the gentle tones of _Hey Jude_ escaping her lips.

**Notes for the Chapter:**

> I'm so sorry, I didn't realize how much more I had written! There are plans for more, it'll just take a bit of time, I'm working on the second ending to Expiration Date and work is draining but there will be more! Please let me know what you think!


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